2,4,5-Trifluoroaniline → HCID 178422803, compound

HRID 1898458Notes

Reaction equation

HRID 1898458 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][C:10]1[NH:11][C:12]2[C:18]3[CH2:19][C:20]([CH3:23])([CH3:22])[O:21][C:17]=3[C:16]([C:24]([O:26]C)=O)=[CH:15][C:13]=2[N:14]=1.[F:28][C:29]1[CH:35]=[C:34]([F:36])[C:33]([F:37])=[CH:32][C:30]=1[NH2:31].C[Al](C)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][C:10]1[NH:11][C:12]2[C:18]3[CH2:19][C:20]([CH3:23])([CH3:22])[O:21][C:17]=3[C:16]([C:24]([NH:31][C:30]3[CH:32]=[C:33]([F:37])[C:34]([F:36])=[CH:35][C:29]=3[F:28])=[O:26])=[CH:15][C:13]=2[N:14]=1

Participants

5

Reactant 3

HCID 949532,4,5-TrifluoroanilineHCID 16682925TrimethylaluminumHCID 178496994HCID 178496994, compound

Product 1

HCID 178422803HCID 178422803, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound was prepared following the procedure described for Example-137 by using methyl 2-[(2-chloro-6-fluorophenyl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylate (Step-1 of Intermediate-15, 0.100 g, 0.256 mmol), 2,4,5-trifluoroaniline (0.056 g, 0.383 mmol), trimethyl aluminium (2M solution in toluene) (0.5 mL), dry toluene (5.0 mL) to afford 0.050 g of the desired product. 1HNMR (DMSO-d6): δ 1.55 (s, 6H), 3.15 (s, 2H), 7.34 (m, 2H), 7.41 (m, 1H), 7.51 (br s, 1H), 7.73 (q, J=10.8 Hz, 10.8 Hz, 1H), 8.54 (m, 1H), 10.13 (s, 1H), 11.27 (br s, 2H); MS [M+H]+: 505.08.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-833fe468e5694464923b612b188b6dc3
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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